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This study examines whether the association between parenting styles and adolescent adjustment reflects universal principles or culturally embedded processes, comparing adolescents from Germany (n = 395) and Spain (n = 331). Grounded in the bidimensional model of parental socialization (warmth × strictness), four styles were identified: authoritative, indulgent, authoritarian, and neglectful. Participants (Mage = 15.6 years) completed measures of parental socialization (ESPA29) and multidimensional self-concept (AF5); academic achievement was obtained from school records, and substance use was self-reported. A cross-sectional design was employed using multivariate analyses of variance that revealed warmth was positively associated with all self-concept domains and negatively with substance use, whereas strictness showed weak or negative links. Significant Parenting Style × Country interactions emerged for academic self-concept, achievement, and substance use. In Spain, indulgent parenting showed particular advantages, especially for academic self-concept. In Germany, both indulgent and authoritative styles yielded favorable outcomes, with authoritative parenting demonstrating protective effects against substance use. These findings question the presumed universal superiority of the authoritative style and underscore the cultural embeddedness of optimal parenting, supporting a contextualist model of adolescent socialization across European contexts.